


A Night Out

by ughsastiel



Series: Sastiel Drabbles [2]
Category: Supernatural
Genre: Friendship, Gen, androgynous!sam, cross dressing
Language: English
Status: Completed
Published: 2014-06-02
Updated: 2014-06-02
Packaged: 2018-02-03 04:37:21
Rating: General Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 723
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1731383
Author URL: https://archiveofourown.org/users/ughsastiel/pseuds/ughsastiel





	A Night Out

Sam had always love the theatre, it gave him a short escape from life on the road. Whenever he and Dean stopped at a big city on their nonstop pre-college road trip which Sam adequately renamed ‘Dean’s Pre-college Panic’. Sam knew it’d be hard for both of them to separate after almost eighteen years of being nearly attached at the hip but it was something Sam had to do for himself. 

The theatre also gave him one more escape. It was the only time he felt like he could escape the almost suffocating hyper masculinity Dean created. Sam was able to style his hair in just the right way so it does that thing where it curls right at the edge. He’s finally able to get out the small sparkled plastic box he kept all his stolen make up in. Whether it was from the pretty girl down the street’s bathroom or from his mother’s purse it was his now and he cherished every single shade of eyeshadow or tube of glossy lip coloring. Once Sam adorned all the makeup and dressed in just the right outfit was when she felt transform. She finally felt comfortable in her oversized, body. At least during the night.

Sam waited for Dean to leave for his favorite sport of picking up the prettiest girl in the bar and bringing her back to the room. Sam implored him to tonight since he knew he’d be out. Dean grinned when Sam gave him the go ahead and quickly left before Sam could change his mind.

Sam watched the clock, waiting for his ten minute safety time to be up. He couldn’t risk being in the middle of getting ready when Dean came back for some forgotten item. Once fifteen minutes past Sam found himself in front of the mirror with his small plastic box. He flipped the tiny metal clasps on the front and flipped it open. 

It felt natural as the eyeshadow dusted his lids and the pink tinted lipstick glossed over his lip, accentuating his thin upper lip. He struggled with the eyeliner and mascara but after ten minutes of effort he finally did the wings perfectly. Sam blinked a few times in disbelief at her face. Or his face, it was starting to shift into the gray area between as he got his outfit out. He had picked out a light blue, fitted sweater which toned down his broad shoulders and brought attention to his naturally slim waist. Sam had shaved his legs this morning while Dean slept so he could put on a pencil skirt that hugged his hips perfectly.

Finally, she was finished. Her hair, makeup and outfit was absolutely perfect. There was no other word she could think of to describe it. She rushed to grabbed her phone and purse before calling a cab. 

The theater house was packed, patrons spilled in from all angles. Sam was a little self conscious of her size, even wearing flats she towered over a good portion of the men. She shuffled into the theater, keeping herself small with slouched shoulders as she made the rest of the trek to her seat.   
The lights flickered signaling all the patrons to get to their seats. Sam got out her phone in order to silence it, She heard someone clear their throat above her and looked up. 

A girl around Sam’s age stood in front of her and looked obviously nervous.

“Um, hello. I believe you’re in my seat.” She said timidly.

“Oh really. My ticket says B19.” Sam furrowed her brows.

“Yes and that’s B18.” She pointed to the small plaque on the arm rest. Sam’s face went red in embarrassment and she quickly hopped over a seat.

“I’m so sorry. I didn’t mean to take your sat.” Sam said bashfully.

“Oh its alright. I’m Castiel by the way.” She smiled.

“It’s nice to meet you. I’m Sam. You look really lovely in your dress.” Sam returned the smiled. The dress really was stunning, a part of Sam was jealous the she didn’t have the lean frame needed to pull it off.

“It’s nice to meet you too. May I ask how you got your hair to flip like that? With all the humidity, I can barely tame mine, let alone style it.”

“Yeah, I’d love that.”


End file.
